NO764110L - - Google Patents
Info
- Publication number
- NO764110L NO764110L NO764110A NO764110A NO764110L NO 764110 L NO764110 L NO 764110L NO 764110 A NO764110 A NO 764110A NO 764110 A NO764110 A NO 764110A NO 764110 L NO764110 L NO 764110L
- Authority
- NO
- Norway
- Prior art keywords
- aromatic
- stated
- reaction
- carried out
- amine
- Prior art date
Links
- -1 aromatic urethanes Chemical class 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- PBBJBFOOHLPWOV-UHFFFAOYSA-N 1,1'-biphenyl;carbonic acid Chemical compound OC(O)=O.C1=CC=CC=C1C1=CC=CC=C1 PBBJBFOOHLPWOV-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 125000004104 aryloxy group Chemical group 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- TXSLQCZKCZCCAS-UHFFFAOYSA-N ethyl n-(4-chlorophenyl)-n-methylcarbamate Chemical compound CCOC(=O)N(C)C1=CC=C(Cl)C=C1 TXSLQCZKCZCCAS-UHFFFAOYSA-N 0.000 description 1
- ZHMIEJHAMNTUBZ-UHFFFAOYSA-N ethyl n-phenyl-n-propylcarbamate Chemical compound CCOC(=O)N(CCC)C1=CC=CC=C1 ZHMIEJHAMNTUBZ-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/40—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings
- C07C271/42—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C271/44—Esters of carbamic acids having oxygen atoms of carbamate groups bound to carbon atoms of six-membered aromatic rings with the nitrogen atoms of the carbamate groups bound to hydrogen atoms or to acyclic carbon atoms to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
Foreliggende oppfinnelse vedrører en fremgangsmåte for fremstilling av aromatiske uretaner med den generelle formel The present invention relates to a method for the production of aromatic urethanes with the general formula
hvori Ar er et radikal inneholdende minst en aromatisk gruppe av typen fenyl, naftyl, eventuelt substituert med alkyl,. alkoksy, in which Ar is a radical containing at least one aromatic group of the type phenyl, naphthyl, optionally substituted with alkyl. Alkoxy,
aryl, aryloksy, halogener eller dialkylamino, og R og R' er like eller forskjellige og er alkylradikaler eller hydrogenatomer. aryl, aryloxy, halogens or dialkylamino, and R and R' are the same or different and are alkyl radicals or hydrogen atoms.
Det er kjent å syntetisere angjeldende forbindelser ved å gå utIt is known to synthesize the compounds in question by exiting
fra deres respektive fenoler og alkylisocyanater, eller også fra arylklorformater og aminer, som kjent fra f.eks. italiensk patent-skrift 965.506-from their respective phenols and alkyl isocyanates, or also from aryl chloroformates and amines, as known from e.g. Italian patent document 965.506-
Disse tidligere metoder medfører-i tillegg til at de er meget omstendelige betraktelige usikkerhetsmomenter med hensyn til giftigheten av de2eaksjonskomponenter som anvendes. In addition to being very laborious, these previous methods involve considerable uncertainties with regard to the toxicity of the de2eaction components used.
Det er likeledes kjent at de angjeldende produkter finner hyppig anvendelse innenfor industrien som insektisider, hvorav noen er spesielt interessante på grunn av deres lave giftighetsindeks. It is also known that the products in question find frequent use within the industry as insecticides, some of which are particularly interesting because of their low toxicity index.
Det er nå funnet at det er mulig å oppnå slike forbindelser vedIt has now been found that it is possible to obtain such compounds by
å omsette aromatiske karbonater med alifatiske aminer, eventuelt i nærvær av organiske løsningsmidler. Reaksjonen finner sted spontant og hurtig, endog under meget milde betingelser inntil karbonatet er blitt fullstendig omdannet, ved anvendelse av støkiometrisd mengder av aminet. to react aromatic carbonates with aliphatic amines, possibly in the presence of organic solvents. The reaction takes place spontaneously and rapidly, even under very mild conditions until the carbonate has been completely converted, using stoichiometric amounts of the amine.
Et overskudd av aminet, eller en for høy temperatur (over 100°C) kan føre til dannelse av en viss mengde urea som biprodukt. An excess of the amine, or too high a temperature (above 100°C) can lead to the formation of a certain amount of urea as a by-product.
De følgende eksempler skal illustrere oppfinnelsen.The following examples shall illustrate the invention.
EKSEMPEL 1EXAMPLE 1
107 g bifenylkarbonat og 150 ml benzen ble innført i en 500 ml kolbe. 30 g rent propylamin ble gradvis innført i blandingen idet temperaturen ble holdt i området rundt 40°C. 107 g of biphenyl carbonate and 150 ml of benzene were introduced into a 500 ml flask. 30 g of pure propylamine was gradually introduced into the mixture, keeping the temperature in the region of around 40°C.
Det ble oppnådd 86g fenyl-propyluretan med et utbytte på omtrent 95% av det teoretiske. 86g of phenyl-propyl urethane was obtained with a yield of approximately 95% of the theoretical.
EKSEMPEL 2EXAMPLE 2
160 g binaftylkarbonat og 150 ml dioksan ble innført i en 500 ml kolbe. 160 g of binaphthyl carbonate and 150 ml of dioxane were introduced into a 500 ml flask.
16 g rent gassformet metylamin ble boblet gjennom blandingen i16 g of pure gaseous methylamine was bubbled through the mixture i
1 time idet temperaturen ble holdt ved 20°C.1 hour while the temperature was kept at 20°C.
Det ble oppnådd 93 g alfa-naftyl-alfametyl uretan.93 g of alpha-naphthyl-alphamethyl urethane was obtained.
EKSEMPEL 3EXAMPLE 3
140 g 4,4'-dikloro-bifenyl-karbonat og 150 ml CC14ble innført i en 50 0 ml kolbe. 16 g rent metylamin ble tilsatt mens temperaturen ble holdt ved 30°C. 140 g of 4,4'-dichloro-biphenyl carbonate and 150 ml of CCl 4 were introduced into a 500 ml flask. 16 g of pure methylamine were added while maintaining the temperature at 30°C.
Det ble oppnådd 85 g 4-kloro-fenyl-N-metyl uretan. 85 g of 4-chloro-phenyl-N-methyl urethane were obtained.
Claims (3)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT29960/75A IT1051034B (en) | 1975-12-03 | 1975-12-03 | PROCEDURE FOR THE PREPARATION OF AROMATIC URETANS |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NO764110L true NO764110L (en) | 1977-06-06 |
Family
ID=11228760
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NO764110A NO764110L (en) | 1975-12-03 | 1976-12-01 |
Country Status (22)
| Country | Link |
|---|---|
| US (1) | US4097676A (en) |
| JP (1) | JPS5271443A (en) |
| AU (1) | AU509444B2 (en) |
| BE (1) | BE849070A (en) |
| BR (1) | BR7608198A (en) |
| CA (1) | CA1088093A (en) |
| DD (1) | DD127477A5 (en) |
| DE (1) | DE2654939A1 (en) |
| DK (1) | DK538676A (en) |
| FR (1) | FR2333779A1 (en) |
| GB (1) | GB1532028A (en) |
| IE (1) | IE44472B1 (en) |
| IT (1) | IT1051034B (en) |
| LU (1) | LU76300A1 (en) |
| MW (1) | MW4776A1 (en) |
| NL (1) | NL7613526A (en) |
| NO (1) | NO764110L (en) |
| PT (1) | PT65921B (en) |
| SE (1) | SE433610B (en) |
| YU (1) | YU290376A (en) |
| ZA (1) | ZA766992B (en) |
| ZM (1) | ZM13976A1 (en) |
Families Citing this family (17)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4258200A (en) * | 1980-03-11 | 1981-03-24 | Air Products And Chemicals, Inc. | Production of carboxylic acid amides and carbamates using cobalt catalysts |
| JPS60215660A (en) * | 1984-04-11 | 1985-10-29 | Nippon Tokushu Noyaku Seizo Kk | Preparation of biphenylsulfonylurea derivative, intermediate therefor and preparation of said intermediate |
| JPS61134367A (en) * | 1984-12-06 | 1986-06-21 | Nippon Tokushu Noyaku Seizo Kk | Improved production of phenyl n-(2-biphenilylsulfonyl) carbamate |
| IT1183332B (en) * | 1985-02-08 | 1987-10-22 | Enichem Sintesi | PROCEDURE FOR THE PRODUCTION OF N-METHYL CARBAMATES |
| JP2007211029A (en) * | 1997-02-14 | 2007-08-23 | Ube Ind Ltd | Carbamate manufacturing method |
| WO1998035936A1 (en) * | 1997-02-14 | 1998-08-20 | Ube Industries, Ltd. | Process for producing aryl carbamates |
| TWI361179B (en) * | 2006-11-17 | 2012-04-01 | Asahi Kasei Chemicals Corp | A process for producing isocyanates |
| TW200844080A (en) * | 2007-01-11 | 2008-11-16 | Asahi Kasei Chemicals Corp | Process for producing isocyanate |
| JP2007224046A (en) * | 2007-05-23 | 2007-09-06 | Ube Ind Ltd | Carbamate production method |
| JP5313164B2 (en) | 2007-11-19 | 2013-10-09 | 旭化成ケミカルズ株式会社 | Method for producing isocyanate and aromatic hydroxy compound |
| US8895774B2 (en) * | 2008-05-15 | 2014-11-25 | Asahi Kasei Chemicals Corporation | Process for producing isocyanates using diaryl carbonate |
| KR20130127550A (en) * | 2008-05-15 | 2013-11-22 | 아사히 가세이 케미칼즈 가부시키가이샤 | Process for producing isocyanate |
| KR101332485B1 (en) | 2009-08-21 | 2013-11-26 | 아사히 가세이 케미칼즈 가부시키가이샤 | Method of production of n-substituted carbamic acid ester and method of production of isocyanate therefrom |
| EP2679575B1 (en) | 2011-02-21 | 2019-04-10 | Asahi Kasei Kabushiki Kaisha | Process for producing carbonyl compounds |
| CN106349110A (en) * | 2015-07-17 | 2017-01-25 | 大东树脂化学股份有限公司 | Two-stage method and one-pot synthesis method for preparing aliphatic diisocyanate |
| WO2018212206A1 (en) | 2017-05-15 | 2018-11-22 | 旭化成株式会社 | Isocyanate production method |
| US20240425448A1 (en) | 2021-11-08 | 2024-12-26 | Asahi Kasei Kabushiki Kaisha | Method for producing isocyanate compound, method for producing carbamate compound, method for recovering amine compound, and isocyanate composition |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL267254A (en) * | 1960-07-20 | |||
| CH513822A (en) * | 1968-05-25 | 1971-10-15 | Bayer Ag | Process for the preparation of indanyl-N-methylcarbamic acid esters |
-
1975
- 1975-12-03 IT IT29960/75A patent/IT1051034B/en active
-
1976
- 1976-11-19 AU AU19801/76A patent/AU509444B2/en not_active Expired
- 1976-11-22 US US05/744,109 patent/US4097676A/en not_active Expired - Lifetime
- 1976-11-23 ZA ZA766992A patent/ZA766992B/en unknown
- 1976-11-24 CA CA266,423A patent/CA1088093A/en not_active Expired
- 1976-11-26 YU YU02903/76A patent/YU290376A/en unknown
- 1976-11-29 GB GB49727/76A patent/GB1532028A/en not_active Expired
- 1976-11-29 MW MW47/76A patent/MW4776A1/en unknown
- 1976-11-30 DK DK538676A patent/DK538676A/en not_active Application Discontinuation
- 1976-12-01 NO NO764110A patent/NO764110L/no unknown
- 1976-12-01 DD DD196062A patent/DD127477A5/xx unknown
- 1976-12-01 LU LU76300A patent/LU76300A1/xx unknown
- 1976-12-02 PT PT65921A patent/PT65921B/en unknown
- 1976-12-02 FR FR7636338A patent/FR2333779A1/en active Granted
- 1976-12-02 BR BR7608198A patent/BR7608198A/en unknown
- 1976-12-03 NL NL7613526A patent/NL7613526A/en not_active Application Discontinuation
- 1976-12-03 DE DE19762654939 patent/DE2654939A1/en active Pending
- 1976-12-03 SE SE7613628A patent/SE433610B/en unknown
- 1976-12-03 ZM ZM139/76A patent/ZM13976A1/en unknown
- 1976-12-03 IE IE2666/76A patent/IE44472B1/en unknown
- 1976-12-03 JP JP51144819A patent/JPS5271443A/en active Pending
- 1976-12-03 BE BE172977A patent/BE849070A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| YU290376A (en) | 1982-05-31 |
| BR7608198A (en) | 1977-11-22 |
| DE2654939A1 (en) | 1977-06-16 |
| US4097676A (en) | 1978-06-27 |
| FR2333779A1 (en) | 1977-07-01 |
| DD127477A5 (en) | 1977-09-28 |
| PT65921A (en) | 1977-01-01 |
| AU1980176A (en) | 1978-05-25 |
| SE7613628L (en) | 1977-06-04 |
| ZA766992B (en) | 1977-10-26 |
| BE849070A (en) | 1977-06-03 |
| SE433610B (en) | 1984-06-04 |
| JPS5271443A (en) | 1977-06-14 |
| DK538676A (en) | 1977-06-04 |
| PT65921B (en) | 1978-06-13 |
| IT1051034B (en) | 1981-04-21 |
| IE44472B1 (en) | 1981-12-16 |
| AU509444B2 (en) | 1980-05-15 |
| GB1532028A (en) | 1978-11-15 |
| CA1088093A (en) | 1980-10-21 |
| ZM13976A1 (en) | 1977-09-21 |
| MW4776A1 (en) | 1978-02-08 |
| LU76300A1 (en) | 1977-06-09 |
| IE44472L (en) | 1977-06-03 |
| NL7613526A (en) | 1977-06-07 |
| FR2333779B1 (en) | 1980-06-20 |
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